EDIT: To further clarify this, the way Mobile Safari handles <input type="file" /> is to simply grey out the controls, in an attempt to tell you that this is not possible.It's misleading, and stupid, but that's how it is.

Douglas:
I was actually just digging into this a bit more on SMF (I should have researched first).

While this thread implies that it's a Safari limitation, I also came across this thread, which seems to have figured a way around the upload limitations via an auto detection script (and a different theme) in combination to a Modification package being installed.

With the fact that iPhones and iPads encompassing a very significant share of the smart device market, I think it's time that SMF look for a resolution on this issue and includes native support (via smart detection) for Apple products, especially given that the iPad3 is now out, and it's clear that the iP* devices aren't going anywhere, for a while. ::grins::

Please consider this as a legitimate bug report with a request for resolution.

I will test out other forum packages to see if these issues exist and report back.

EDIT: Issue is also present on vBulletin. Maybe we need to step it up and be amongst one of the first forum software packages to also natively support smart devices? :)